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Benzamide → N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide

HRID 68658
ノート
印刷プレビュー

反応式

HRID 68658 の反応式
CNCCNC.I[C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[N:15]=2)[N:10]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:9]=1.[C:39]([NH2:47])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH:26]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:15]=[C:16]3[C:8]([NH:47][C:39](=[O:46])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:9][N:10]([S:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[C:11]3=[N:12][CH:13]=2)=[CH:18][CH:19]=1)(=[O:24])=[O:25])([CH3:27])[CH3:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 2331BenzamideHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 667631397-Iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine

生成物 1

HCID 71143663N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide収率 37.4%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
95 °C

実験手順

CuI (95 mg, 0.4988 mmol), and N,N′-dimethylethane-1,2-diamine (176 mg, 1.997 mmol) in dioxane (5 mL) was heated for 5 minutes at 100° C. in a microwave. 1 mL of this solution was added to a mixture of 7-iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine (100 mg, 0.1720 mmol), benzamide (104.2 mg, 0.8600 mmol) and K3PO4 (73.02 mg, 0.344 mmol) in dioxane (1 mL) and the solution was heated at 95° C. for 1 hour. The reaction mixture is concentrated in vacuo. The residue was partitioned between DCM and water. Combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo yielding an oil which was purified by prep HPLC to give the sub-title product (37 mg, 37%). MS (ES+) 575.1.

後処理

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customyielding an oil which
  7. customwas purified by prep HPLC

出典と根拠

ORDレコード
ord-c9d1960d0ea24e88ab301818a7fa4b81
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822469B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート